1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol | 28435-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol
• 英文别名: 1-deoxy-1,4-imino-D-galactofuranose；1,4-dideoxy-1,4-imino-D-galactitol；1,4-dideoxy-1,4-imino-D-galacitol；(2S,3S,4S)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol
• CAS: 28435-60-1
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: RVNSAAIWCWTCTJ-BGPJRJDNSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  448.6±40.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,5,6-tetra-O-benzyl-D-galactofuranose
  参考文献：
  名称：

  Galf模拟物作为抗结核药的设计，合成和生物活性评估

  摘要：

  合成了一系列新颖的Galf模拟物，并通过IR，（1）H NMR，（13）C NMR，质谱和元素分析对其进行了表征。筛选所有新制备的化合物的抗结核活性。生物活性测定表明，大多数Galf模仿物表现出良好的抗结核活性。特别是化合物4d和4e表现出显着的抗结核功效，与乙胺丁醇相当。

  DOI：

  10.1016/j.carres.2015.11.002
• 作为产物：
  描述：

  [(3S,4S,5S)-1-acetyl-4-benzoyloxy-5-[(1S)-1-hydroxy-2-[(4-methoxyphenyl)methoxy]ethyl]pyrrolidin-3-yl] benzoate 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol
  参考文献：
  名称：

  Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides

  摘要：

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.003

文献信息

• INHIBITORS OF UDP-GALACTOPYRANOSE MUTASE
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20170258805A1

  公开（公告）日：2017-09-14

  Compounds and salts thereof which are acyl-sulfonamides or certain carboxylic acids and which inhibit microbial growth or attenuate the virulence of pathogenic microorganisms and which inhibit UDP-galactopyranose mutase (UGM). Compounds of the invention include 2-aminothiazoles and triazolothiadiazines, particularly 3,6,7-substituted-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, and 2-amino and salts thereof. Methods for inhibiting growth or attenuating virulence of microbial pathogens including mycobacterium , for example, M. tuberculosis and M. smegmatis and Klebsiella , for example, Klebsiella pneumoniae . Methods for inhibiting eukaryotic human and animal pathogens, and fungi and nematodes in particular. Methods for treatment of infections by prokaryotic and eukaryotic pathogens employing compounds of the invention.

  其酰基磺酰胺或某些羧酸的化合物及其盐，能够抑制微生物生长或减弱病原微生物的毒力，并且能够抑制UDP-半乳糖吡喃糖异构酶（UGM）。该发明的化合物包括2-氨基噻唑和三唑噻二嗪，特别是3,6,7-取代的7H-[1,2,4]三唑噻二嗪和其盐，以及2-氨基。抑制微生物病原体生长或减弱其毒力的方法包括结核分枝杆菌（例如结核分枝杆菌和平滑分枝杆菌）和克雷伯氏菌（例如肺炎克雷伯氏菌）等微生物病原体。抑制真核人类和动物病原体、真菌和线虫的方法，特别是治疗原核和真核病原体感染的方法，采用了该发明的化合物。
• Synthesis and investigation of polyhydroxylated pyrrolidine derivatives as novel chemotypes showing dual activity as glucosidase and aldose reductase inhibitors
  作者：Lorenzo Guazzelli、Felicia D'Andrea、Stefania Sartini、Francesco Giorgelli、Gianluca Confini、Luca Quattrini、Ilaria Piano、Susanna Nencetti、Elisabetta Orlandini、Claudia Gargini、Concettina La Motta

  DOI：10.1016/j.bioorg.2019.103298

  日期：2019.11

  Diabetes is a multi-factorial disorder that should be treated with multi-effective compounds. Here we describe the access to polyhydroxylated pyrrolidines, belonging to the d-gluco and d-galacto series, through aminocyclization reactions of two differentially protected d-xylo-hexos-4-ulose derivatives. The prepared compounds proved to inhibit both alpha-glucosidase, responsible for the emergence of

  糖尿病是一种多因素疾病，应使用多种有效化合物治疗。在这里，我们描述了获得多羟基吡咯烷，属于d -葡萄糖和d -半乳糖系列，通过两个差异保护的aminocyclization反应d -低聚木糖-hexos-4酮糖的衍生物。所制备的化合物被证实既抑制了导致高血糖尖峰出现的α-葡萄糖苷酶，又抑制了糖尿病组织异常发展的醛糖还原酶。因此，它们显示出双重抑制谱，被认为是糖尿病治疗的理想选择。明显地，化合物17b 当在类似感光体的661w细胞系中进行测试时，可减少细胞死亡的过程并恢复氧化应激的生理水平，从而证明在糖尿病性视网膜病变的体外模型中有效。
• Aziridine carboxylate from d-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition
  作者：Dilip D. Dhavale、K. S. Ajish Kumar、Vinod D. Chaudhari、Tarun Sharma、Sushma G. Sabharwal、J. PrakashaReddy

  DOI：10.1039/b509216g

  日期：——

  intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the alpha-hydroxy-beta-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively. The glycosidase inhibitory activity of the title compounds was evaluated.

  D-葡萄糖衍生的氮丙啶羧酸酯5是由（E）-乙基-6-溴-1,2-O-异亚丙基-3-O-苄基-5-脱氧-α-D-二甲苯基5-eno-庚烷获得的通过共轭添加苄胺和原位分子内亲核性驱除溴来生成四氢呋喃核苷4。使用水作为亲核试剂的区域选择性氮丙啶开环导致产生α-羟基-β-氨基酯6，该α-羟基-β-氨基酯6分别用于合成六元和五元氮杂糖1b / 1c和2b / 2c。评价了标题化合物的糖苷酶抑制活性。
• Total Synthesis of Azasugar 1,4-Dideoxy-1,4-imino-D-galacitol
  作者：Partha Sarathi Sadhu、Amlipur Santhoshi、Vaidya Jayathirtha Rao

  DOI：10.5012/bkcs.2012.33.11.3554

  日期：2012.11.20

  A new highly stereoselective synthesis of pyrrolidine azasugar 1,4-dideoxy-1,4-imino-D-galacitol is being reported herein. The synthesis was achieved in a linear sequence and inexpensive chiral source (+)-diethyl tartarate was used as the starting material. The key step involved during the synthesis was Pd catalysed amino cyclization of alkenylamine, Bose modified Mitsunobu reaction and Sharpless asymmetric dihydroxylation.

  本文报道了吡咯烷氮糖1,4-二脱氧-1,4-亚氨基-D-半乳糖醇的新的高度立体选择性合成。该合成以线性顺序实现，并且使用廉价的手性源(+)-酒石酸二乙酯作为起始材料。合成过程中涉及的关键步骤是Pd催化的烯胺氨基环化、Bose修饰的Mitsunobu反应和Sharpless不对称二羟基化。
• Inhibitors of UDP-galactopyranose mutase
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US10080757B2

  公开（公告）日：2018-09-25

  Compounds and salts thereof which are acyl-sulfonamides or certain carboxylic acids and which inhibit microbial growth or attenuate the virulence of pathogenic microorganisms and which inhibit UDP-galactopyranose mutase (UGM). Compounds of the invention include 2-aminothiazoles and triazolothiadiazines, particularly 3,6,7-substituted-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, and 2-amino and salts thereof. Methods for inhibiting growth or attenuating virulence of microbial pathogens including mycobacterium, for example, M. tuberculosis and M. smegmatis and Klebsiella, for example, Klebsiella pneumoniae. Methods for inhibiting eukaryotic human and animal pathogens, and fungi and nematodes in particular. Methods for treatment of infections by prokaryotic and eukaryotic pathogens employing compounds of the invention.

  本发明的化合物及其盐类为酰基磺酰胺类或某些羧酸类，可抑制微生物生长或减弱病原微生物的毒力，并可抑制UDP-半乳糖吡喃糖突变酶（UGM）。本发明的化合物包括 2-氨基噻唑和三唑并噻二嗪，特别是 3,6,7-取代的-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪及其 2-氨基和盐。抑制微生物病原体生长或减弱其毒性的方法，这些微生物病原体包括分枝杆菌（例如结核杆菌和烟曲霉菌）和克雷伯氏菌（例如肺炎克雷伯氏菌）。抑制真核人类和动物病原体，特别是真菌和线虫的方法。利用本发明化合物治疗原核和真核病原体感染的方法。